CN114829332A - 制备二酯类材料的方法 - Google Patents
制备二酯类材料的方法 Download PDFInfo
- Publication number
- CN114829332A CN114829332A CN202180005264.4A CN202180005264A CN114829332A CN 114829332 A CN114829332 A CN 114829332A CN 202180005264 A CN202180005264 A CN 202180005264A CN 114829332 A CN114829332 A CN 114829332A
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- reactor
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- alcohol
- diester
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- 239000000463 material Substances 0.000 title claims abstract description 61
- 150000005690 diesters Chemical class 0.000 title claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 238
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 64
- 238000000034 method Methods 0.000 claims abstract description 35
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
- 230000032050 esterification Effects 0.000 claims description 17
- 238000005886 esterification reaction Methods 0.000 claims description 17
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 6
- 238000010924 continuous production Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 12
- 230000003247 decreasing effect Effects 0.000 abstract description 11
- 239000004014 plasticizer Substances 0.000 description 14
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 9
- OEIWPNWSDYFMIL-UHFFFAOYSA-N dioctyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C=C1 OEIWPNWSDYFMIL-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 230000007613 environmental effect Effects 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 5
- 241000183024 Populus tremula Species 0.000 description 4
- 229940088597 hormone Drugs 0.000 description 4
- 239000005556 hormone Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 3
- -1 etc. Chemical compound 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003609 titanium compounds Chemical class 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- BMASLOOHTMQIGP-ZOKJKDLISA-H (z)-but-2-enedioate;butyltin(3+) Chemical compound CCCC[Sn+3].CCCC[Sn+3].[O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O BMASLOOHTMQIGP-ZOKJKDLISA-H 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- UJMZZAZBRIPOHZ-UHFFFAOYSA-N 2-ethylhexan-1-ol;titanium Chemical compound [Ti].CCCCC(CC)CO UJMZZAZBRIPOHZ-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 231100000049 endocrine disruptor Toxicity 0.000 description 1
- 239000000598 endocrine disruptor Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 241000894007 species Species 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
- C07C69/82—Terephthalic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2020-0153956 | 2020-11-17 | ||
| KR1020200153956A KR20220067352A (ko) | 2020-11-17 | 2020-11-17 | 디에스터계 물질의 제조방법 |
| PCT/KR2021/011084 WO2022108050A1 (ko) | 2020-11-17 | 2021-08-20 | 디에스터계 물질의 제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114829332A true CN114829332A (zh) | 2022-07-29 |
Family
ID=81709274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202180005264.4A Pending CN114829332A (zh) | 2020-11-17 | 2021-08-20 | 制备二酯类材料的方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20220371984A1 (de) |
| EP (1) | EP4023628A4 (de) |
| JP (1) | JP2023507538A (de) |
| KR (1) | KR20220067352A (de) |
| CN (1) | CN114829332A (de) |
| WO (1) | WO2022108050A1 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20240047325A (ko) * | 2022-10-04 | 2024-04-12 | 한화솔루션 주식회사 | 에스테르계 조성물의 제조 방법 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5095138A (en) * | 1989-10-06 | 1992-03-10 | Societe Nationale Elf Aquitaine (Production) | Continuous synthesis of mercaptocarboxylic acid esters |
| CN1118158A (zh) * | 1993-01-19 | 1996-03-06 | 埃克森化学专利公司 | 生产增塑剂和多醇酯的方法 |
| CN1478115A (zh) * | 2000-12-21 | 2004-02-25 | �������˹��ĭ�ۺ���ɷ�����˾ | 连续生产聚酯或共聚酯的方法 |
| US20110251420A1 (en) * | 2008-12-16 | 2011-10-13 | Basf Se | Method for producing carboxylic acid esters |
| CN102442905A (zh) * | 2010-10-12 | 2012-05-09 | 中国石油化工股份有限公司 | 连续酯化制备己二酸二甲酯的方法 |
| JP2018052993A (ja) * | 2018-01-12 | 2018-04-05 | 三菱ケミカル株式会社 | アクリル酸ブチルの製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7799942B2 (en) * | 2005-08-12 | 2010-09-21 | Eastman Chemical Company | Production of terephthalic acid di-esters |
| TWI654177B (zh) * | 2013-10-31 | 2019-03-21 | 德商巴斯夫歐洲公司 | 製備羧酸酯的方法及其作爲塑化劑的用途 |
| KR101663586B1 (ko) * | 2016-04-28 | 2016-10-10 | 애경유화주식회사 | 차별화 된 반응 온도 제어를 이용하여 반응 전환 속도를 높인 디옥틸테레프탈레이트의 제조방법 |
| KR102138788B1 (ko) | 2017-09-07 | 2020-07-28 | 주식회사 엘지화학 | 에스터 조성물의 제조 시스템 및 이를 이용한 에스터 조성물의 제조 방법 |
| CN107935846B (zh) * | 2017-11-03 | 2020-01-10 | 中国林业科学研究院林产化学工业研究所 | 一种连续化生产环保型增塑剂的装置和方法 |
| KR102325729B1 (ko) * | 2018-11-28 | 2021-11-15 | 주식회사 엘지화학 | 가압 구간을 포함하는 테레프탈레이트계 조성물의 제조방법 |
| WO2020204558A1 (ko) * | 2019-04-04 | 2020-10-08 | 주식회사 엘지화학 | 에스터계 조성물의 제조방법 및 제조 시스템 |
-
2020
- 2020-11-17 KR KR1020200153956A patent/KR20220067352A/ko not_active Application Discontinuation
-
2021
- 2021-08-20 EP EP21854731.3A patent/EP4023628A4/de active Pending
- 2021-08-20 CN CN202180005264.4A patent/CN114829332A/zh active Pending
- 2021-08-20 US US17/635,925 patent/US20220371984A1/en active Pending
- 2021-08-20 JP JP2022511391A patent/JP2023507538A/ja active Pending
- 2021-08-20 WO PCT/KR2021/011084 patent/WO2022108050A1/ko unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5095138A (en) * | 1989-10-06 | 1992-03-10 | Societe Nationale Elf Aquitaine (Production) | Continuous synthesis of mercaptocarboxylic acid esters |
| CN1118158A (zh) * | 1993-01-19 | 1996-03-06 | 埃克森化学专利公司 | 生产增塑剂和多醇酯的方法 |
| CN1478115A (zh) * | 2000-12-21 | 2004-02-25 | �������˹��ĭ�ۺ���ɷ�����˾ | 连续生产聚酯或共聚酯的方法 |
| US20110251420A1 (en) * | 2008-12-16 | 2011-10-13 | Basf Se | Method for producing carboxylic acid esters |
| CN102442905A (zh) * | 2010-10-12 | 2012-05-09 | 中国石油化工股份有限公司 | 连续酯化制备己二酸二甲酯的方法 |
| JP2018052993A (ja) * | 2018-01-12 | 2018-04-05 | 三菱ケミカル株式会社 | アクリル酸ブチルの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2023507538A (ja) | 2023-02-24 |
| EP4023628A4 (de) | 2023-09-20 |
| WO2022108050A1 (ko) | 2022-05-27 |
| KR20220067352A (ko) | 2022-05-24 |
| US20220371984A1 (en) | 2022-11-24 |
| EP4023628A1 (de) | 2022-07-06 |
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